Chicago is well-known for many things from iconic foods, to the famous Cloud Gate (aka “The Bean”), to local art and culture. Whether you’re in the market for a home in Chicago, an apartment with a view, or a rental house in one of the many neighborhoods, The Windy City is ready to dazzle you with all it has to offer.
1. Traverse the city by water taxi
The Chicago Water Taxi comes recommended from local photographer Saverio Truglia Photography. “Perhaps one of the most unique and affordable ways to see Chicago. This unguided commute through the heart of the city offers breathtaking views of Chicago’s skyline from a different perspective. Take it round trip or just one way.”
2. Cool down with a cone
“It is a tradition for my team to grab an ice cream cone from Jeni’s Splendid Ice Creams after long wedding days. Not only do they make the craziest, most amazing flavors you could ever imagine, but they have mastered the classics,” shares Alyssa of Northwest Weddings, a Chicago-based wedding coordination and planning company. “We highly recommend heading to the Fulton Market location for great ice cream and great music in the heart of Chicago.”
3. Discover community in every corner
One of the most unique things you can do in Chicago is simply strolling through the many neighborhoods of the city. Marissa, owner and wedding photographer at Marissa K Webb Photography says Chicago thrives on its neighborhoods, each corner of the city fostering its own vibrant community. “The West Loop, for instance, represents the perfect blend of the city’s industrial past and its modern creative pulse. This is where spaces like the Little Goat Diner become more than just a restaurant—they transform into venues for celebration and connection.”
4. Visit a Windy City Winery
The Bronzeville Winery, known for its “cool vibe,” seamlessly blends art, culture, and community while offering an exceptional selection of food, cocktails, and wine accompanied by live entertainment. Whether you’re enjoying locally sourced food or sipping on wines highlighting the craft of female and minority winemakers, it’s a perfect spot to experience the rich history and vibrant future of Chicago.
5. Wander west for a classic Italian meal seasoned with love
Chef Arturo, originally from Ecuador, has called Chicago home since he was 20 years old. At his beloved restaurant, Mirabella Italian Cuisine & Bar, you’ll find family warmth, old-school Italian dishes, and the best-grilled calamari in town. Chef Arturo’s passion makes Mirabella a true Chicago gem.
6. Get up close with nature
There is something for every nature lover at The Peggy Notebaert Nature Museum. Located in the heart of Lincoln Park, Chicagoans of all ages can connect with the wonders of nature and science. Meet local turtles through animal encounters, experience the tropical free-flying butterflies and moths of the Judy Istock Butterfly Haven, and discover more amazing adventures the museum has to offer.
7. Mix it up with your inner bookworm
Make sure to check out New Book Joy “Booktique” and head to one of their monthly Mix + Mingle events for another unique activity to do in Chicago. Their gatherings provide a true taste of Chicagoland culture, from books and reading pairings to drinks, food, music, and more from small businesses. Swing by an open house to meet new people in the community and get a taste of their featured local businesses such as lobster rolls from Une Année, Old Bay Chips from Snack Lab, mini fruit tarts from Bee My Honey Sweets + Treats, and summer wine tastings from Bottles & Cans. They even have some bookish events coming up for kids to enjoy, too.
8. Indulge in historical luxury
For a quintessential Chicago experience, visit The Blackstone Hotel, famously known as the ‘Hotel of Presidents.’ Built in 1910 with stunning Beaux-Arts architecture, this historic landmark has hosted presidents and celebrities alike. Located in the heart of the arts and theater district, it’s the perfect spot to immerse yourself in Chicago’s history while exploring nearby Millennium Park.
9. Taste the magic of the Mediterranean in all four seasons
Since opening in late summer 2018, Le Sud Mediterranean Kitchen has become a favorite with Roscoe Village neighbors and friends from across the city and suburbs. Their spacious sidewalk café becomes fully enclosed in the winter season, giving guests an iconic outdoor dining experience from them year-round.
10. Unwind with Happy Hour at a local bar
If you’re looking for a unique cocktail experience, check out Golden Years in Chicago. This West Town cocktail bar offers the feel-good Rock and Blues of the 70s, along with modern takes on the fun cocktails of the day. They also offer a daily happy hour and the best Toki Highball in the city.
11. Take in the culture through diverse art exhibitions
Just a quick Metra ride outside the city, the small-but-mighty Elmhurst Art Museum has a rotating exhibition schedule that compares to world-class museums and is situated on the gorgeous Wilder Park in the Elmhurst neighborhood, a sprawling and walkable outdoor retreat. While you’re on the museum campus, check out the McCormick House, an idyllic 1950s home design by the iconic 20th century architect Mies van der Rohe.
12. Explore the east side with authentic Italian dining
Chicago Prime Italian is a must-visit in the suburbs of Schaumburg. This family-owned gem offers comfort Italian fare made with fresh organic ingredients, house-made sauces, and pastas, alongside prime steaks, fresh seafood, and an award winning wine list. With a beautiful patio for seasonal outdoor dining and a welcoming atmosphere, it’s an ideal spot for any occasion.
13. Visit the variety of parks in the city
Miguel of MNPhotoStudios recommends these beautiful places to visit for little or no cost:
- Lincoln Park: Not only is it home to breathtaking views of the city skyline, the Lincoln Park Zoo in its midst has all kinds of animals, and it is free to enter every day.
- Millennium Park: The must-see park full of unique spots, summer concerts, and, of course, the well-known Cloud Gate. This is definitely a Chicago bucket list item you’ll need to check off your list as a new resident.
- Chicago Botanic Garden: This vast and beautiful botanic garden located just outside the city is definitely worth the drive and entry fee to see the variety of different trees and flowers they have to showcase.
Unique things to do in Chicago: Final thoughts
From open-ended wanderings to personalized experiences, living in Chicago offers something for everyone. The vibrant and inclusive community makes it a great place to explore or put down new roots. No matter what brings you to the Windy City, these 13 unique things to do in Chicago are just the tip of the iceberg when it comes to this city.
